Arylpyrrole carbonitrile compounds are highly effective insecticidal, acaricidal and nematocidal agents with a unique mode of action and a broad spectrum of activity. In particular, 2-aryl-5-(trifluoromethyl)pyrrole-3-carbonitrile compounds demonstrate effective control across a wide array of pests and can control resistant pests such as pyrethroid-, organophosphate-, cyclodiene-, organochlorine-, organotin-, carbamate-, and benzophenylurea-resistant biotypes of Helicoverpa/Heliothis spp., Spodoptera spp., Trichoplusia spp., Pseudoplusia spp. and Tetranychus spp. Because there is no apparent cross-resistance, 2-aryl-5-trifluoromethylpyrrole-3-carbonitrile compounds and their derivatives have potential for use in resistance management programs. Further, said pyrroles have little effect on beneficial species making them excellent candidates for integrated pest management programs, as well. These programs are essential in today's crop production.
Therefore, methods to prepare said pyrroles and intermediates to facilitate their manufacture are of great value. Among the present methods to prepare 2-aryl-5-trifluoromethylpyrrole-3-carbonitrile compound on a manufacturing scale is the 1,3-dipolar cycloaddition of 3-oxazolin-5-one with 2-chloroacrylonitrile (U.S. Pat. No. 5,030,735).
It is an object of this invention to provide 5-amino-4-aryl-2-perfluoroalkyl-1,3-oxazole derivatives useful as key intermediates in the manufacture of insecticidal, acaricidal and nematocidal pyrrole compounds.
It is another object of this invention to provide a facile method of preparation of said oxazole intermediates.
It is a further object of this invention to provide an alternate source of important intermediate compounds and manufacturing routes for the production of a new class of highly effective pesticidal compounds.